Semi Private Deep Wine Chianti and San Gimignano from Florence

Recommended by 97% of travelers

Badge of Excellence

Florence, Italy

Great choice

10+ bookings last month.

8 hours 30 minutes (approx.)
Pickup offered
Mobile ticket
Offered in: English

Why travelers loved this

4.9

· Amy_F ·

Sep 2025

All aspects of this excursion were enjoyable…the vineyards, the San Gimignano stop, and lots of delicious food and wine! Our driver was very friendly and knowledgeable, and we were grateful for the small group dynamic. Nice to have someone else do all the planning and driving. Vehicle was very comfortable.

· Sheri_N ·

Jul 2026

We loved this tour. We had enough time in San Gimignano to stroll around and shop and didn’t feel rushed. The lunch was amazing with several courses and the wineries had fabulous Chianti wine. You will probably want to ship some home kind of good! This tour is worth the price and the small group made it better.

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Overview

Escape the crowds and discover the inspiring landscapes and famous flavors of the Chianti wine region on a small-group tour from Florence. Enjoy leisure time to explore the charming medieval town of San Gimignano with helpful pointers from your guide. Visit local wineries for tours, followed by a tasting of renowned Chianti varietals along with a traditional Tuscan lunch.

Taste Chianti's famed varietals at a local winery
Savor locally made products such as cheese, salami and olive oil
Get a more personalized experience on a small-group tour
Skip the need for taxis with hassle-free hotel pickup and drop-off

What's Included

One unlimited Wi-Fi Pocket-Sized Hotspot for each couple. Stay connected throughout your journey.
Wine tasting and olive oil tasting
Lunch

You'll enjoy a delicious Tuscan lunch with some of the best local food you can find, and it will be paired with some of the finest Chianti wines.
Alcoholic Beverages

We make sure you will get a taste of various Chianti wines before going home. Our tour includes tasting of wines so you can sample the different flavors of this popular Italian wine.
WiFi on board
Air-conditioned vehicle
1 Bottle of Prosecco White Wine per group
Bottled water
Hotel pick up and drop off is included within the pickup zone

Gratuity
Hotel pick up and drop off out of the pick up zone is available under request for an extra fee

Meeting and Pickup

You can head directly to the meeting point, or request pickup

Pickup points

Select a pickup point

Pickup details

We offer free pick up at hotels, not Airbnb nor apartments, which are located in the AREA A of the traffic limited zone. If your hotel is outside that area or falls in the category of Apartments/Airbnb, you can choose to receive free pick up in front of HOTEL BOCCACCIO (Via della Scala 59) at 8:00 or in front of HOTEL DAVANZATI (Via Porta Rossa 5) at 7:50. Alternatively we can pick you up and drop you off at your hotel for an extra fee to be paid directly to the driver. Ask for quotation. However, please arrive 15 minutes before scheduled departure time at the pickup point.

Meeting point

Hotel Boccaccio
Via della Scala, 59, 50123 Firenze FI, Italy
The tour starts at 8:00. Please show up at the meeting point 15 minutes in advance.

End point

This activity ends back at the meeting point.

Start time
.8:00 am

Itinerary

Piazzale Michelangelo

15 minutes • Admission Ticket Free

San Gimignano

1 hour 25 minutes • Admission Ticket Free

San Casciano in Val di Pesa

2 hours 30 minutes • Admission Ticket Free

San Michele a Torri

45 minutes • Admission Ticket Free

Florence (Pass By)

Additional Info

Confirmation will be received at time of booking
A maximum of 8 people per Mercedes van
Wheelchair accessible
Stroller accessible
Near public transportation

Infant seats available
Most travelers can participate
Direct pick up and drop off from some hotels locates in the historic center (A zone). For all other locations private residences and B&B the meeting points is: In front of Hotel Boccaccio-Tino Caffè, Via della Scala 59 (one minute walking distance from Santa Maria Novella train station), Florence at 8,00 am. Please arrive 15 minutes before scheduled departure time. If you wish you can have breakfast there, English or continental or just a "cappuccino". As I Just Drive guests at Tino Caffè you are entitled to have a 10% discount.
This tour/activity will have a maximum of 8 travelers

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Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Featured review

Kathryn_D

My husband and I absolutely loved this experience and would do it again in a heartbeat! Our driver Sara was lovely and such a pleasure to be around. Each location was allocated the perfect amount of time and it was a great way to escape Florence for the day. The trip to San Gimignano was the perfect amount of time to explore the local shops. Gelato Dondoli was recommended to us by Sara and it did not disappoint. Such unique flavors, truly some of the best gelato we had during our trip to Italy! We stopping in Le Tori a.r.l. for some leather shopping and it was a wonderful experience. The woman who helped us was knowledgeable and took the time to explain different aspects of the leather and craftsmanship to us. There are also some lovely linen clothing stores there as well. The entire experience at Castillo Monterinaldi was phenomenal. Andrea led us on the tour and wine tasting. The tour was lovely, Andrea was knowledgeable and answered any questions we had. The wine tasting was one of the best experiences. The food was unreal and the wine pairings were perfection. I also have a severe food allergy and they were extremely accommodating and understanding. The tour at the second vineyard was lovely. It was a smaller wine operation than the first vineyard. We were lead through an olive oil and wine tasting. The Chianti was paired with a beautiful selection of meats and cheeses from the farm. If we were staying in Italy longer I would have loved to have purchased some.

Reviews

4.9

based on 215 reviews

Total reviews and rating from Viator & Tripadvisor

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San Gimignano/Winery Tour Must Do

Sheri_N, Jul 2026

This was a lovely tour!...

Sara_S, Jun 2026

This was a lovely tour! Our guide was David, who was an absolute joy to ride along with and to learn from. The two wineries were perfect - excellent wine tastings paired with a delicious lunch and selection of Tuscan meats & cheeses. The San Gimignano portion of the trip was not for us as it is really just a place to shop. But if you want to do some shopping, there are a large variety of cute shops and you’d likely enjoy it. Either way that is just a short piece of the tour. Highly recommend both this tour and specifically David!

Incredible day

Candace_G, Apr 2026

Such a great experience. Our driver, Claudius was fantastic and extremely Informative about local areas. The wineries were absolutely beautiful

Just ok

Susan_M, Mar 2026

The trip was fun, in my opinion overpriced for the experience. Our tour guide was nice, but spoke so fast It was difficult to understand him. The lunch was just okay, wine was delicious.

Wonderful

Emily_H, Mar 2026

Leonardo was wonderful. Absolutely beautiful day, a LOT of wine, a delicious lunch, a beautiful city, and wonderful memories. Thank you!!

Response from Host, Mar 2026

Dear Emily, Thank you so much for your beautiful words and for choosing our family business. It truly means a lot to us to know that your day in Chianti and San Gimignano was filled with such special moments. We are genuinely happy to hear that Leonardo made your experience so enjoyable and that you were able to fully appreciate the beauty of the landscapes, the wine, and the lunch along the way. Creating days like these, rich in memories, is exactly what we hope to offer every guest. Your kind message will be shared with Leonardo, and we know it will make him smile. We hope to welcome you again one day for another unforgettable experience. Warm regards

Sensational trip

Joanne_D, Feb 2026

This experience was exceptional. Our driver Gabriel was amazing, enthusiastic, engaging and informative about the various destinations. We visited 2 wineries and found the level of information, food/lunch superb and wines extremely interesting. We also visited San Girimingao loved it. Couldn’t ask for a better trip.

Great Day Trip.

Melinda_F, Sep 2025

It was a great day trip. Our driver Francisco was awesome! Very knowledgeable of the Area, and personable. We had a four course lunch at the first winery. (That took a bit long for us) we learned at both wineries and the wine at both were great

Excellent experience

Amy_F, Sep 2025

Great tour

Kathryn_L, Aug 2025

Fantastic! Fantastic! If you’re going to do one tour in Florence make it this one. If you can book with Diana, we met at 8am and left with a friend in Italy at 5. Great food and wine and very knowledgeable about the area. I can’t recommend this trip enough just book it!

My husband and I...

Kathryn_D, Jul 2025

Amazing experience 10/10

John_M, Jun 2025

Gabriel was excellent. Friendly and informative. He was an excellent driver and guide. The vineyards were great. I really can't say enough good things. We had an incredible day. This was a highlight of our trip.

Good, but not our favorite

Juliet_M, Jun 2025

It was a good day in Tuscany. The stops were well worth it, however there was less wine tasting than I would have hoped for the price. We’ve done several wine tours in many countries and this was unfortunately not one of my favorites. We did two tours in Florence and we both preferred the other to this one. It was nice to have a small group, but I would look elsewhere for a little more laid back free form tasting.

Exceptionally personal way to travel through Tuscany

michael_r, May 2025

This is such an intimate and easy way to see what you really want to see. Our driver Claudius was excellent. He explained everything as we went and pointed out all the things that we needed to know would appreciate. The service is over the top and convenient. Would highly recommend if you are looking for a more intimate experience than a big bus tour. Make sure to ask for Claudius too!

Response from Host, May 2025

Dear Guest, Thank you so much for your 5-star review! We're delighted to hear that you enjoyed a more intimate and personal way to explore with us. Claudius will be thrilled to know that his insights and thoughtful attention made your day special. We’re so glad the experience felt easy, informative, and a step above the usual group tour. We truly appreciate your recommendation and hope to welcome you back on another Truescany adventure soon! Warm regards, Brian - Customer Care Manager

Book it!

Margaret_L, Apr 2025

Such a beautiful and fun day. OUr guide Alberto was wonderful and very knowledgeable. We bonded with the other travelers, ate a fabulous luncheon and learned how to really read a label. Loved it!

Tuscany is beautiful.

Paul_A, Mar 2025

This was a great day. Even with cloudy skies, the area was beautiful. Gabrielle, our driver, was very personable and knowledgeable of the area. If you want a day to see an old city and some wineries, this trip and company is for you. I highly recommend taking this tour.

Great time!

bgmangia, Feb 2025

Great day! Andrea was very professional yet personable. Arrived on time. The wineries we went to were beautiful and the representatives were great and very friendly and knowledgeable. Lunch was delicious. As was all the food. Can’t say enough about the tour!

Response from Host, Mar 2025

Dear, We're so glad to hear that you had a great day with Andrea! It’s wonderful that you enjoyed the beautiful wineries, delicious food, and the warm hospitality along the way. Andrea’s professionalism and friendly approach truly make for a memorable experience. Thank you for your kind words—we appreciate your support and would love to welcome you on another tour in the future! Best regards, Brian - Customer Care Manager

Fabulous

Gary_C, Nov 2024

Just very personable and informative. Great tour guide Francisco. Spots were great. Grandaughter really enjoyed the small tour.

Great day trip

Dale_I, Oct 2024

Everything from the meeting was better than expected. Tour guide Sara was lovely & had a good sense of humour. Loved our free time in San Gimignano and gelato recommendation. The countryside was spectacular and the organised lunch and tastings perfect. What a great vibe. Will do it again next time I’m in Florence

Best part of our Italy vacation.

Debbie_W, Oct 2024

We were so happy that our driver made a stop just outside of Florence in order for us to get some amazing photos overlooking the city.

Wonderful experience -- highly recommend!

Gigi_J, Oct 2024

Our guide was terrific very knowledgeable, a great driver and very kind. We stopped on the way to the wineries at an area overlooking Florence were there were breathtaking views of the city. The first winery we visited the host was terrific. Learned a lot about their winemaking process and enjoyed a fabulous meal. It was also fun getting to know the others on our tour. Great experience.

Recommend Semi-Private Experience

Colin_F, Sep 2024

Great chance to experience the Tuscan countryside. San Gimignano was a must-see with a great gelato shop! Wine tasting at two wineries was also good. The semi-private tour was a good compromise between affordability and flexibility.

Excellent experience for...

Derek_D, Sep 2024

Excellent experience for seeing the Chianti countryside and vineyards. Top tier wine tour with a local guide eager to share Tuscan history.

Far but fun!

Martha_H, Sep 2024

Our guide was fun and great. He nade sure we were fine. It is a very winding road, so you can get car sick. We had a great time and had enough time for pictures. The name says it all, it’s deep in Chianti.

Best wine tour!

Daniel_H, Sep 2024

One of the best excursions ever! Sara was so much fun! Entertaining snd informative! Lovely lunch, great wines and beautiful scenery! Do It!!

Highly recommend.

darius_m, Sep 2024

What an awesome tour. Sarah was a fantastic guide that made the trip so worthwhile. We were lucky enough to only have 4 people on the tour and fortunately the other couple were Aussies! Highly recommend this tour as it is personal and good value for money.

Fantastic Experience

Mike_C, Sep 2024

Our Guide, Alberto, was amazing. He catered to our group with incredible hospitality. He knew every aspect of our region and it's deep history. The wineries we visited were something to behold. Stunning properties and very friendly staff. The wine tastings were fantastic. We gained a new found knowledge of the wine making experience and enjoyed some great food. If you can get Alberto as your guide you are lucky. Would definitely book this again.

Fabulous Day

Anthony_T, Aug 2024

A huge THANKYOU to SARA for a wonderful and delightful full day tour on our Private Tuscan Winery Tour. We had an entertaining and informative day. We also had the pleasure & company of 2 fellow Aussies. Great food, wine & very comfortable transport. Thanks again! Anthony & Suzi.

Wonderful Experience in San Gimignano and Chianti

Angelic_A, Jul 2024

Wonderful tour! Sara was fantastic! The food and wine was delicious! Excellent experience! We recommend it.

A must do when in Florence

Peter_F, Jul 2024

This was an amazing experience for our group of 5. Our guides Alberto and Andrea were amazing, truly informative, making all of us confortable, feel welcomed. More than a tour, our guides acted as friends making us discover Tuscany and more specifically the Chianti region, with great stories. A truly worthwhile private tour of two wineries and beautiful San Gimignano. A must do.

Fantastic!

Jeanie_I, Jul 2024

We had a great day in the Tuscan countryside. Amazing food, service, and transportation. Sara was helpful, informative and punctual. The experience was way more than we expected. Definitely recommend!